Air-Stable Organoradical Boron Reagents |
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| Authors: | Zenghui Li Jing Wang Xiaoyang Liu Pin Gao Guoping Li Prof Gang He Prof Bin Rao |
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| Institution: | 1. School of Chemistry, Engineering Research Center of Energy Storage Materials and Devices, Ministry of Education, Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi An Shi, Xi'an, 710049 China;2. Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi An Shi, Xi'an, 710049 China |
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| Abstract: | Both organic radicals and organoboron reagents have been broadly investigated, but the combination of them via direct C−H borylation as organic radical building blocks has never been achieved. Herein, a series of organoradical boron reagents, such as TTM-Bpin and TTM-BOH , were synthesized through the key step of C−H borylation of substrate TTM-H ((2,6-dichlorophenyl) bis(2,4,6-trichlorophenyl)methyl) radical for the first time. They are air stable enough to be stored in the solid state for several months under dark conditions, and fully investigated through single crystal analysis, EPR and DFT calculations. Furthermore, they can smoothly work in the standard Suzuki–Miyaura coupling (SMC) reaction with retention of the carbon radical center. Meanwhile, these radical species bearing different boron units display fluorescent character and are potentially applied for the collective synthesis of luminescent organic radicals, as well as other functionalized open-shell materials. |
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| Keywords: | Air-Stable Radicals C−H Borylation Suzuki–Miyaura Coupling Reaction Triarylmethyl Radicals |
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